Sylvester Stallone confessed during an interview on CBS Sunday Morning at 92NY that his primary life regret is not marrying his wife, Jennifer Flavin, eight years earlier. The 80-year-old actor, who shares three daughters with Flavin, candidly blamed his own past procrastination for the delay.
The Bottom Line
- The Regret: Stallone admitted on CBS Sunday Morning that he wishes he had married Flavin eight years sooner than he actually did.
- The Relationship Timeline: The pair met in a West Hollywood restaurant in 1988, experienced a brief filing for divorce in August 2022 followed by a rapid reconciliation, and officially wed in 1997.
- The Sentiment: Stallone credited Flavin with keeping him alive and teaching him how to love after decades of navigating personal relationships.
Reflecting on Decades of Procrastination in New York
When sit-down host Tracy Smith asked the veteran action star if he ever wished for a “do-over” in his life, Stallone didn’t hesitate. Speaking to the audience on September 27, the man behind iconic cinematic figures like Rocky Balboa pointed directly to his romantic history. “I wish I’d married my wife about eight years earlier,” Stallone confessed. “I was like such an idiot, procrastinating. Because you know, I’m still actually learning about relationships that bad.”
Addressing Flavin directly through the broadcast, the actor added, “So I regret that. And I’m sorry, baby.” Stallone went on to acknowledge that he will “never be as good” as his partner, describing her as “magnificent” and the sole reason he has been kept alive. “And it took me so long to turn my head around and go, ‘Oh, you have the greatest gift in the world right here, and you’re looking out there, you fool!’” he remarked.
From a West Hollywood Encounter to a Nearly Three-Decade Marriage
The romance between Stallone and Flavin stretches back to 1988, when their paths crossed by chance at a restaurant in West Hollywood, California. At the time of their initial meeting, Stallone was 42 years old and Flavin was 19. Looking back at that night during a May 2023 episode of their reality television series, The Family Stallone, the actor remembered the distinct impact of her arrival.
“I remember vividly the first time I met Jennifer. I was in this dark restaurant, a few people. She came in and, whoa! Something happened,” Stallone shared on the program. “I just felt, like, this jolt, like — ‘Oh, did we just have a minor earthquake or something?’” Flavin similarly recalled that they hit it off instantly and remained inseparable throughout the evening.
| Year | Milestone |
|---|---|
| 1988 | First met at a West Hollywood restaurant. |
| 1997 | Officially married after nearly a decade together. |
| 2022 | Briefly filed for divorce in August, followed by a reconciliation one month later. |
| 2026 | Stallone reflects on the relationship during a CBS Sunday Morning interview. |
Learning How to Love After Prior Marriages
Before building his long-term life with Flavin, Stallone walked down the aisle twice. He was previously married to Sasha Czack from 1974 to 1985, and subsequently to Brigitte Nielsen from 1985 to 1987. His journey with Flavin culminated in a wedding ceremony in 1997, though the pair faced a brief test in August 2022 when Flavin filed for divorce before reconciling just one month later.
Reflecting on how his perspective shifted over sixty years, Stallone credited his wife with teaching him the mechanics of genuine affection. “It’s a habit, you know, learning to love, a really wonderful habit,” he explained. “And with my wife, Jennifer, it’s finally come to fruition. It took about 60 years, but we got there.” Today, the couple shares three daughters: Sophia, Sistine, and Scarlet.
